Founding Sales Engineer, AI Infrastructure

Featherless AI; Toronto; On-site; CAD 208,000 - 263,000; Full time

Benefits offered by this job

Competitive base + commission

Job summary

Featherless AI is seeking a Senior Account Executive in Toronto to close enterprise AI deals and build strategic relationships with CTOs, ML leads and infra decision-makers. You will own the full sales cycle from discovery to close, tailoring proposals to customer stack and use case, and collaborating with product and engineering to feed the field.

You’ll forecast pipeline, maintain clean CRM in HubSpot, and mentor BDRs while expanding revenue within existing accounts in a fast-moving AI

Qualifications

• 3–6 years of closing experience in Cloud Infrastructure, MLOps, or AI/developer tooling.
• Proven track record closing deals with developers, ML engineers, CTOs.
• Comfortable navigating multi-stakeholder enterprise sales cycles.
• Strong written and verbal communication with technical literacy.
• Entrepreneurial and self-driven approach to building process.

Responsibilities

• Run full-cycle sales across mid-market and enterprise segments.
• Lead discovery calls and technical demos tailored to buyer stacks.
• Develop custom proposals and business cases connecting model inference needs to Featherless capabilities.
• Negotiate and close complex, multi-stakeholder deals.
• Expand revenue within existing accounts via upsell/cross-sell opportunities.
• Use AI tools to automate research, outreach, and workflow efficiency.
• Maintain CRM hygiene in HubSpot with accurate pipeline
• Collaborate with product and engineering to relay field feedback.
• Mentor BDRs and shape pipeline expectations.

Skills

Closing deals

Enterprise sales

Multi-stakeholder sales

CRM (HubSpot)

Technical buyer communication

Tools

HubSpot

Clay AI

Claude/ChatGPT

Job description

Featherless AI is seeking a Senior Account Executive in Toronto to close enterprise AI deals and build strategic relationships with CTOs, ML leads and infra decision-makers. You will own the full sales cycle from discovery to close, tailoring proposals to customer stack and use case, and collaborating with product and engineering to feed the field.

You’ll forecast pipeline, maintain clean CRM in HubSpot, and mentor BDRs while expanding revenue within existing accounts in a fast-moving AI